Sleepy Hollow Holidays

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Where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas and neighborhoods for the activities you enjoy most. Learn more about Sleepy Hollow
Downtown Chicago featuring a city

Downtown Chicago

4 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotel + flight trips in Downtown Chicago

Top hotels in Sleepy Hollow

River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is Rp2.666.129 per night from 2 Jul to 3 Jul
Rp2.666.129
per night
2 Jul - 3 Jul
8.6/10 Excellent! (2,954 reviews)
"This was such a conveniently located hotel. We were able to walk to so many places. The guy that checked us in was super friendly and set the tone for a really nice stay. I also really appreciated to cold filtered water stations all over to refill our water bottles. I would definitely stay here ..."

Reviewed on 16 Jun 2024

River Hotel
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is Rp2.706.010 per night from 18 Jun to 19 Jun
Rp2.706.010
per night
18 Jun - 19 Jun
7.6/10 Good! (7,009 reviews)
"We were definitely surprised, and not in a good way about how small our room was. We had to shimy between the bed and air conditioner to get to the side of the bed, or crawl on the bed to get to that side."

Reviewed on 17 Jun 2024

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is Rp3.129.112 per night from 2 Jul to 3 Jul
Rp3.129.112
per night
2 Jul - 3 Jul
8/10 Very Good! (2,381 reviews)
"easy to locate in the heart of downtown chicago"

Reviewed on 14 Jun 2024

Embassy Suites by Hilton Chicago Downtown River North
See all 4,314 properties in Sleepy Hollow
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a Sleepy Hollow holiday package cost?
Get your credit card ready, because a getaway to Sleepy Hollow starts from a tempting . When you bundle your flights, hotels and more into a package, you’ll land the lowest prices.
How do I get a cheap travel package to Sleepy Hollow?
Book everything in the one place with our Sleepy Hollow holiday packages. We have incredible bargains on hotels, flights, tours and more that’ll keep your travel budget happy and your adventurous spirit alive. And, with more than 550 partner airlines and 1,000,000 hotel options around the world to pick from, there are endless opportunities to mix and match as you like.
Where should I stay in Sleepy Hollow?
There’s plenty to do in Sleepy Hollow, so stay near its best attractions and spend more time sightseeing. Balzekas Museum of Lithuanian Culture is one spot to put on your must-see list.
How far in advance should I book my Sleepy Hollow holiday?
Reserving your flights early with Expedia means one less thing to worry about. A number of air carriers advertise prices up to 12 months in advance. This is usually the cheapest time to book. If circumstances have left you booking late, fantastic last-minute deals to Sleepy Hollow sometimes emerge a few weeks before departure.
What does an Expedia Sleepy Hollow travel package include?
Expedia has everything you need to lock in Sleepy Hollow trip, but what goes into your package is your call. Select from any combination of rental cars, flights and hotels. Chasing some experiences or tours to keep you on the go? Once you’ve made your booking, you can add them on too. No matter your style, there’s a package to meet your needs.
What should I know before booking a Sleepy Hollow travel package?
Booking all the parts of your getaway together is a great way to save. Bundle your airfares, rental cars and hotels into a neat package. But your options don’t end at hotels. Expedia has all kinds of properties, including holiday rentals like beachside villas and city apartments. You’ve got choices galore!
Can I choose my airline with a Sleepy Hollow Expedia holiday package?
Expedia has access to more than 550 airline partners worldwide, so you definitely can. Simply select the carrier that suits you and craft your ideal Sleepy Hollow getaway.
If I'm not able to travel, can I cancel my Sleepy Hollow holiday package?
Certainly, and we’ll help you every step of the way. You may be able to cancel or amend your Sleepy Hollow holiday package at no cost if you booked in the last 24 hours. But you may incur a fee from your hotel, airline or car rental company for older bookings. If your travel plans unexpectedly change, have a look at our Customer Service Portal for more information.

Popular places to visit

Image for Wrigley Field

Wrigley Field

4.5/5(40 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Image for Six Flags Great America

Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America
Image for Navy Pier

Navy Pier

4/5(125 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

Rp2.040.034
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
Image for Chicago: City Minibus Tour with Optional Architecture Cruise

Chicago: City Minibus Tour with Optional Architecture Cruise

Rp725.988
Per adult
98% of travellers recommend
Chicago: City Minibus Tour with Optional Architecture Cruise
Image for BYOB Spray Paint 'n' Sip at Studio W.I.P. Chicago

BYOB Spray Paint 'n' Sip at Studio W.I.P. Chicago

Rp695.835
Per adult
98% of travellers recommend
BYOB Spray Paint 'n' Sip at Studio W.I.P. Chicago
See all activities in Chicago

More trip options

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.